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WO1998013352A1 - Sels de 2-desoxy-2-amino(ou 2-methylamino)-d-glucose comprenant de l'acide n-arachidonacetique et possedant une activite anti-microbienne - Google Patents

Sels de 2-desoxy-2-amino(ou 2-methylamino)-d-glucose comprenant de l'acide n-arachidonacetique et possedant une activite anti-microbienne Download PDF

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Publication number
WO1998013352A1
WO1998013352A1 PCT/RU1997/000293 RU9700293W WO9813352A1 WO 1998013352 A1 WO1998013352 A1 WO 1998013352A1 RU 9700293 W RU9700293 W RU 9700293W WO 9813352 A1 WO9813352 A1 WO 9813352A1
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WO
WIPO (PCT)
Prior art keywords
acid
deoxy
glucose
application
amino
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/RU1997/000293
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English (en)
Russian (ru)
Inventor
Oleg Viktorovich Travkin
Elena Vladimirovna Yakovleva
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Individual
Original Assignee
Individual
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Priority to AU46401/97A priority Critical patent/AU4640197A/en
Publication of WO1998013352A1 publication Critical patent/WO1998013352A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
    • C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
    • C07D219/06—Oxygen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
    • C07H5/04—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to nitrogen
    • C07H5/06—Aminosugars

Definitions

  • the invention is related to medicine, and specifically, to synthetic biological compounds that are related to the class of derivative amines.
  • the main component (kation) of the claimed compounds is 2-deoxy-2-amine (or 2-methylamine) - ⁇ -glucose.
  • aminosugars are called derivatives of carbohydrates that contain together with single or small-sized hydroxy groups, amine-or amine-alkyl groups.
  • alkylamine was the subject of numerous studies on the manufacture of pharmaceuticals on the basis of them. It is well known, for example, that it has been diagnosed with polio antipyretic drugs (amplucamine), and also has 5
  • the direct biological active component (anion) is acidic acid.
  • connection is the closest structural analogue of the compounds we declare, and it is the price of the connection.
  • the offered by the authors of the connection is identical to the claimed compounds by their acid component, but in the absence of a connection to the car, there is no connection between the patient and the customer. It is known that aminosugar
  • 1-deoxy-1-methylamine-genesis in nature, does not occur, is extremely unstable in industrial products, negatively and highly consumptive.
  • the syntheses of these compounds from natural glucose (glucose, galactose) include a number of working stages, which result in low outputs and in harsh conditions.
  • the metabolic pathway of this compound in the cell has not yet been studied [16,17].
  • Example 1 The method of synthesizing salt is 2-deoxy-2 amine- ⁇ -glucose with pedia-acidic acid. -6-
  • Example 2 The method of synthesizing 2-deoxy-2 methyl methyl- ⁇ -glucose with pedia-acid acid.
  • Table 1 The potent activity of the claimed drugs, cameroda and industrialism in the case of Venezuelan white horse mouse encephalitis.
  • Sections Ya ⁇ 1 and C 13 which are not measured on the H Suginagekeg –200 and supporting connections, are subject to additional charges.
  • Salt of 2-deoxy-2-amine- ⁇ -glucose with pedia-acid acid does not have a clear melting point, above 130 S is slowly charred.
  • ⁇ _0 50 (internal, white mice) is 620 mg / kg
  • 150 g of ⁇ -acid acetic acid dissolves when boiled in 520 ml. 95% ethanol. ⁇ avoiding peregreva, by small rations, within 15 min. on 15 January 2-2-methyl-0-glucose.
  • the resulting mixture is boiled down with a refinery for 30 minutes. and then cool to a temperature of 0-2 C. With this, the lower layer of a thick dark yellow oil is formed.
  • the melting process is higher than 85 ° C and slowly liquefies.
  • the specific excitation coefficient ⁇ °., Cm 194 + 1
  • S 50 (internal, white mice) is 580 mg / kg.
  • mice males weighing 16-18g.
  • the ELD causative agent was administered in doses of 6 and 60 LD50 doses of (1) and (2) drugs, 50 mg / kg was used, and there was a 4-day treatment (-4 hours + 72 hours + 144 hours) Therefore, in comparison with the preparations used, camedone and cycles were used.
  • the efficacy of the pesticides evaluated the death rate of mice.
  • Table 1 As follows from the data presented, the preparations (1) and
  • Table 1 The potent activity of the claimed preparations (1) and (2) is comedy and industrial in the case of the Venezuelan encephalitis in white mouse
  • P ⁇ e ⁇ a ⁇ a ⁇ C ⁇ EMA introduced D ⁇ za D ⁇ za Le ⁇ al Protective d ⁇ niya ⁇ - ⁇ a ⁇ a ⁇ a, vi ⁇ usa, n ⁇ s ⁇ , ⁇ a, ⁇ a ⁇ a ⁇ a hour mg / ⁇ g% LD 50%
  • the drugs were administered to the interior of the muscle and a dose of 50 mg / kg for 4 hours before and for the second day after infection of the laboratory.
  • the products (1) and (2) were used in the form of 10% stable products.
  • the drug was used rbamidil (virazole), which was given to the patients in a medical treatment for 100 mg / dose.
  • the data obtained are presented in table 2.
  • mice weighing 18-20g.
  • the juvenile scheme (- 4; + 48; +120).
  • the drugs were used in the same doses, but in combination with gentamicin. Antibiotics were started after 1 day after infection of the mice ⁇ , the drug was administered intramuscularly for 8 days at a dose of 5 mg / kg. fifteen
  • Us ⁇ an ⁇ vlen ⁇ ( ⁇ abl.Z) ch ⁇ claimed ⁇ e ⁇ a ⁇ a ⁇ y, vzya ⁇ ye in ⁇ deln ⁇ s ⁇ i ⁇ a ⁇ iches ⁇ i ⁇ azyvayu ⁇ not influence ⁇ echenie ⁇ nevm ⁇ v ⁇ y in ⁇ e ⁇ tsii mice ⁇ dna ⁇ in ⁇ mbinatsii with gen ⁇ amitsin ⁇ m d ⁇ s ⁇ ve ⁇ n ⁇ ⁇ vyshayu ⁇ zaschi ⁇ n ⁇ e deys ⁇ vie e ⁇ g ⁇ 0 an ⁇ ibi ⁇ i ⁇ a.
  • the product did not exert any influence, either in isolation or in combination with antibiotics.
  • the drugs (1), (2) and the drug compared the cycles introduced internally at a dose of 100 mg / kg.
  • the treatment with the medical treatment scheme (- 48; - 24; +2 hours). 2.
  • the preparations were used in the same doses, but in combination with the intramuscular administration of the antibiotic ampicillin at a dose of 5 mg / mouse.
  • the claimed compounds are new, non-obvious and intentionally applicable, i.e. Meets all the requirements of the invention.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Communicable Diseases (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Oncology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Cette invention concerne des composés synthétiques et actifs sur le plan biologique, lesquels appartiennent à la classe des dérivés d'aminoglucose. Cette invention concerne plus précisément des sels de 2-désoxy-2-amino(ou 2-méthylamino)-D-glucose comprenant de l'acide N-arachidonacétique, lesquels possèdent une activité anti-microbienne et correspondent à la formule générale (I) où R représente -H ou -CH3. Cette invention concerne également des formules chimique et structurelle, des exemples de synthèses, ainsi que des résultats d'expériences biologiques menées sur des modèles de bactéries et de virus contenant de l'ADN et de l'ARN.
PCT/RU1997/000293 1996-09-26 1997-09-24 Sels de 2-desoxy-2-amino(ou 2-methylamino)-d-glucose comprenant de l'acide n-arachidonacetique et possedant une activite anti-microbienne Ceased WO1998013352A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU46401/97A AU4640197A (en) 1996-09-26 1997-09-24 2-deoxy-2-amino(or 2-methylamino)-d-glucose salts comprising n-arachidonacetic acid and showing anti-microbial activity

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
RU96118754 1996-09-26
RU9696118754A RU2093510C1 (ru) 1996-09-26 1996-09-26 Соли 2-дезокси-2-амино (или 2-метиламино)-d-глюкозы с n-акридонуксусной кислотой, обладающие противомикробной активностью

Publications (1)

Publication Number Publication Date
WO1998013352A1 true WO1998013352A1 (fr) 1998-04-02

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PCT/RU1997/000293 Ceased WO1998013352A1 (fr) 1996-09-26 1997-09-24 Sels de 2-desoxy-2-amino(ou 2-methylamino)-d-glucose comprenant de l'acide n-arachidonacetique et possedant une activite anti-microbienne

Country Status (3)

Country Link
AU (1) AU4640197A (fr)
RU (1) RU2093510C1 (fr)
WO (1) WO1998013352A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002074311A1 (fr) * 2001-03-20 2002-09-26 Oleg Viktorovich Travkin Preparation medicinale antitumorale, antivirale, antibacterienne, antiparasitaire, anti-inflammatoire, antifongique et immunomodulatrice, procede de fabrication et formes de medicaments
RU2404773C2 (ru) * 2008-12-04 2010-11-27 Закрытое акционерное общество "Биологические исследования и системы" Фармацевтическая композиция на основе акридонуксусной кислоты и ее соединений для лечения гнойно-деструктивных поражений слизистой и кожи, общесистемных заболеваний при иммунодефицитных состояниях

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2135474C1 (ru) * 1998-08-19 1999-08-27 Травкин Олег Викторович Соли 1-дезокси-1-n-метиламиногексаспиртов с n-акридонуксусной кислотой, обладающие иммуномодулирующей активностью, и лекарственное средство на их основе

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3912714A (en) * 1973-04-09 1975-10-14 Valter Osvaldovich Kulbakh N-methyl-d-clucosamine complex of 4-methyluracil, method for producing and use thereof
EP0214642A2 (fr) * 1985-09-09 1987-03-18 Orion-Yhtymä Oy Fermion Sels complexes de glucosaminesulfate et leur procédé de préparation
RU2036198C1 (ru) * 1993-04-01 1995-05-27 Товарищество с ограниченной ответственностью "Полисан" N-МЕТИЛ-N-( α,D -ГЛЮКОПИРАНОЗИЛ) АММОНИЯ-2-(АКРИДОН-9-ОН-10-ИЛ)АЦЕТАТ(ЦИКЛОФЕРОН), ОБЛАДАЮЩИЙ ИНТЕРФЕРОНОГЕННОЙ, ПРОТИВОВИРУСНОЙ, В ТОМ ЧИСЛЕ АНТИВИЧ, АНТИПАРАЗИТАРНОЙ, АНТИПРОМОТОРНОЙ И РАДИОПРОТЕКТИВНОЙ АКТИВНОСТЬЮ

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3912714A (en) * 1973-04-09 1975-10-14 Valter Osvaldovich Kulbakh N-methyl-d-clucosamine complex of 4-methyluracil, method for producing and use thereof
EP0214642A2 (fr) * 1985-09-09 1987-03-18 Orion-Yhtymä Oy Fermion Sels complexes de glucosaminesulfate et leur procédé de préparation
RU2036198C1 (ru) * 1993-04-01 1995-05-27 Товарищество с ограниченной ответственностью "Полисан" N-МЕТИЛ-N-( α,D -ГЛЮКОПИРАНОЗИЛ) АММОНИЯ-2-(АКРИДОН-9-ОН-10-ИЛ)АЦЕТАТ(ЦИКЛОФЕРОН), ОБЛАДАЮЩИЙ ИНТЕРФЕРОНОГЕННОЙ, ПРОТИВОВИРУСНОЙ, В ТОМ ЧИСЛЕ АНТИВИЧ, АНТИПАРАЗИТАРНОЙ, АНТИПРОМОТОРНОЙ И РАДИОПРОТЕКТИВНОЙ АКТИВНОСТЬЮ

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002074311A1 (fr) * 2001-03-20 2002-09-26 Oleg Viktorovich Travkin Preparation medicinale antitumorale, antivirale, antibacterienne, antiparasitaire, anti-inflammatoire, antifongique et immunomodulatrice, procede de fabrication et formes de medicaments
RU2197248C2 (ru) * 2001-03-20 2003-01-27 Травкин Олег Викторович Лекарственный препарат, обладающий иммуномоделирующим, иммунокоррегирующим, противопаразитарным, противосклеротическим, противовирусным, противобактериальным, противогрибковым, противовоспалительным и противоопухолевым действием, и способ его приготовления
RU2404773C2 (ru) * 2008-12-04 2010-11-27 Закрытое акционерное общество "Биологические исследования и системы" Фармацевтическая композиция на основе акридонуксусной кислоты и ее соединений для лечения гнойно-деструктивных поражений слизистой и кожи, общесистемных заболеваний при иммунодефицитных состояниях

Also Published As

Publication number Publication date
AU4640197A (en) 1998-04-17
RU2093510C1 (ru) 1997-10-20

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